JPS6254781B2 - - Google Patents
Info
- Publication number
- JPS6254781B2 JPS6254781B2 JP53119123A JP11912378A JPS6254781B2 JP S6254781 B2 JPS6254781 B2 JP S6254781B2 JP 53119123 A JP53119123 A JP 53119123A JP 11912378 A JP11912378 A JP 11912378A JP S6254781 B2 JPS6254781 B2 JP S6254781B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- catalyst
- mmol
- distillation
- solvent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 46
- 239000003054 catalyst Substances 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 39
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 27
- 238000009835 boiling Methods 0.000 claims description 22
- UIKQNMXWCYQNCS-UHFFFAOYSA-N 2-hydroxybutanal Chemical class CCC(O)C=O UIKQNMXWCYQNCS-UHFFFAOYSA-N 0.000 claims description 19
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 19
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 239000007810 chemical reaction solvent Substances 0.000 claims description 13
- 229910052703 rhodium Inorganic materials 0.000 claims description 13
- 239000010948 rhodium Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 13
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 12
- 150000003003 phosphines Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 238000004821 distillation Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 19
- 239000000126 substance Substances 0.000 description 16
- 238000000926 separation method Methods 0.000 description 15
- 238000007037 hydroformylation reaction Methods 0.000 description 14
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- AXPZIVKEZRHGAS-UHFFFAOYSA-N 3-benzyl-5-[(2-nitrophenoxy)methyl]oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC1OC(=O)C(CC=2C=CC=CC=2)C1 AXPZIVKEZRHGAS-UHFFFAOYSA-N 0.000 description 10
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 7
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- PIAOXUVIBAKVSP-UHFFFAOYSA-N γ-hydroxybutyraldehyde Chemical compound OCCCC=O PIAOXUVIBAKVSP-UHFFFAOYSA-N 0.000 description 4
- JTMCAHGCWBGWRV-UHFFFAOYSA-N 3-hydroxy-2-methylpropanal Chemical compound OCC(C)C=O JTMCAHGCWBGWRV-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004803 Di-2ethylhexylphthalate Substances 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- PWATWSYOIIXYMA-UHFFFAOYSA-N Pentylbenzene Chemical compound CCCCCC1=CC=CC=C1 PWATWSYOIIXYMA-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 229910052734 helium Inorganic materials 0.000 description 2
- 239000001307 helium Substances 0.000 description 2
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- -1 polyester Chemical class 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- UPGSWASWQBLSKZ-UHFFFAOYSA-N 2-hexoxyethanol Chemical compound CCCCCCOCCO UPGSWASWQBLSKZ-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- YFNONBGXNFCTMM-UHFFFAOYSA-N butoxybenzene Chemical compound CCCCOC1=CC=CC=C1 YFNONBGXNFCTMM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- FYTVHPJPJIHZBS-UHFFFAOYSA-N ethyl-pentyl-phenylphosphane Chemical compound CCCCCP(CC)C1=CC=CC=C1 FYTVHPJPJIHZBS-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11912378A JPS5545646A (en) | 1978-09-29 | 1978-09-29 | Preparation of hydroxybutylaldehyde |
| US06/069,850 US4275243A (en) | 1978-09-29 | 1979-08-27 | Process for producing hydroxybutyraldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11912378A JPS5545646A (en) | 1978-09-29 | 1978-09-29 | Preparation of hydroxybutylaldehyde |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5545646A JPS5545646A (en) | 1980-03-31 |
| JPS6254781B2 true JPS6254781B2 (it) | 1987-11-17 |
Family
ID=14753499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11912378A Granted JPS5545646A (en) | 1978-09-29 | 1978-09-29 | Preparation of hydroxybutylaldehyde |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4275243A (it) |
| JP (1) | JPS5545646A (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03186285A (ja) * | 1989-12-16 | 1991-08-14 | Harumi Hiuga | 運動競技コートライン識別灯及び電源コントロールボックス付屋内競技場の床 |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1166270A (en) * | 1981-04-30 | 1984-04-24 | Mitsuo Matsumoto | Method of producing 1,9-nonanedial and/or 9-hydroxy-7- nonen-1-al |
| JPS58157739A (ja) * | 1982-03-12 | 1983-09-19 | Kuraray Co Ltd | １，９−ノナンジア−ルの製造方法 |
| JPS606630A (ja) * | 1983-06-24 | 1985-01-14 | Kuraray Co Ltd | アリルアルコ−ルの連続ヒドロホルミル化方法 |
| US4594463A (en) * | 1985-01-28 | 1986-06-10 | Union Carbide Corporation | Synthesis of aldehydes from alcohols |
| US4613701A (en) * | 1985-09-19 | 1986-09-23 | Celanese Corporation | Recovery of rhodium from hydroformylation reaction product |
| DE3534317A1 (de) * | 1985-09-26 | 1987-04-02 | Ruhrchemie Ag | Verfahren zur herstellung von nonadecandiolen |
| US5043480A (en) * | 1989-06-29 | 1991-08-27 | Eastman Kodak Company | Difunctional products from ethylene oxide and synthesis gas |
| JP2775907B2 (ja) * | 1989-07-12 | 1998-07-16 | 三菱化学株式会社 | ヒドロホルミル化法 |
| US5198589A (en) * | 1992-04-28 | 1993-03-30 | The United States Of America As Represented By The United States Department Of Energy | Cobalt carbonyl catalyzed olefin hydroformylation in supercritical carbon dioxide |
| US20050161644A1 (en) * | 2004-01-23 | 2005-07-28 | Peng Zhang | Immersion lithography fluids |
| TWI259319B (en) * | 2004-01-23 | 2006-08-01 | Air Prod & Chem | Immersion lithography fluids |
| EP3445318A1 (en) | 2016-04-22 | 2019-02-27 | Innospec Limited | Methods, compositions and uses relating thereto |
| JPWO2021045153A1 (it) * | 2019-09-06 | 2021-03-11 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129412A (en) * | 1974-08-30 | 1976-03-12 | Kuraray Co | Butanjioorurui no seizohoho |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515757A (en) * | 1966-04-01 | 1970-06-02 | Ethyl Corp | Organic compounds and processes |
| US3511880A (en) * | 1966-09-16 | 1970-05-12 | Union Oil Co | Hydrocarbonylation process |
| US3946082A (en) * | 1972-03-24 | 1976-03-23 | Exxon Research & Engineering Co. | Preparation of zerovalent phosphine substituted rhodium compounds and their use in the selective carbonylation of olefins |
| US4064145A (en) * | 1975-10-20 | 1977-12-20 | Celanese Corporation | Production of tetrahydrofuran |
| JPS5278809A (en) * | 1975-12-26 | 1977-07-02 | Ube Ind Ltd | Preparation of 1, 4-butanediol |
-
1978
- 1978-09-29 JP JP11912378A patent/JPS5545646A/ja active Granted
-
1979
- 1979-08-27 US US06/069,850 patent/US4275243A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129412A (en) * | 1974-08-30 | 1976-03-12 | Kuraray Co | Butanjioorurui no seizohoho |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03186285A (ja) * | 1989-12-16 | 1991-08-14 | Harumi Hiuga | 運動競技コートライン識別灯及び電源コントロールボックス付屋内競技場の床 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5545646A (en) | 1980-03-31 |
| US4275243A (en) | 1981-06-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6254781B2 (it) | ||
| US4311851A (en) | Preparation of carboxylic acid esters with BF3 -alcohol complex catalyst | |
| JPS6221771B2 (it) | ||
| JPS60218341A (ja) | グリコ−ルアルデヒドを経由するエチレングリコ−ルの製造方法 | |
| US5177278A (en) | Preparation of cyclododecene | |
| US4761492A (en) | Process for recovering trimethoxysilane from a trimethoxysilane and methanol mixture | |
| JPS6331450B2 (it) | ||
| US3968133A (en) | Carboxylation process for preparing linear fatty acids or esters | |
| US5292917A (en) | Process for purifying dimethyl carbonate | |
| EP0295361B1 (en) | Preparation of pseudoionones | |
| EP0501374B1 (en) | Process for purifying dimethyl carbonate | |
| JPS6157814B2 (it) | ||
| US4676874A (en) | Separation of n-propyl acetate from n-propanol and water by extractive distillation | |
| JP2002535321A (ja) | ホルミルテトラヒドロフラン及びその水和物の混合物水溶液の製造 | |
| US4262138A (en) | Preparation of carboxylic acid esters with BF3 complex catalyst | |
| US4843172A (en) | Process for preparing α-phenylpropionic acid derivative | |
| US6429340B1 (en) | Process for producing 2,4,5,-trialkylbenzaldenhydes | |
| US4967019A (en) | Method of manufacturing 2-propyn-1-ol | |
| EP0314434A1 (en) | Rhodium recovery from hydroformylation reaction product | |
| US4365079A (en) | Recovery of dimethyl sebacate from an isomeric mixture of C12 esters | |
| JPH0251552B2 (it) | ||
| EP0097891B1 (en) | A method for refining crude aldehyde products | |
| JP2841689B2 (ja) | バレルアルデヒドの精製法 | |
| JP3864617B2 (ja) | アルコールの製造方法 | |
| JP2824113B2 (ja) | ２―ヒドロキシテトラヒドロフランの製造方法 |